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Enantioselective benzylic C–H arylation via photoredox and nickel dual catalysis

The asymmetric cross-coupling reaction is developed as a straightforward strategy toward 1,1-diaryl alkanes, which are a key skeleton in a series of natural products and bioactive molecules in recent years. Here we report an enantioselective benzylic C(sp(3))−H bond arylation via photoredox/nickel d...

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Autores principales: Cheng, Xiaokai, Lu, Huangzhe, Lu, Zhan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6685991/
https://www.ncbi.nlm.nih.gov/pubmed/31391466
http://dx.doi.org/10.1038/s41467-019-11392-6
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author Cheng, Xiaokai
Lu, Huangzhe
Lu, Zhan
author_facet Cheng, Xiaokai
Lu, Huangzhe
Lu, Zhan
author_sort Cheng, Xiaokai
collection PubMed
description The asymmetric cross-coupling reaction is developed as a straightforward strategy toward 1,1-diaryl alkanes, which are a key skeleton in a series of natural products and bioactive molecules in recent years. Here we report an enantioselective benzylic C(sp(3))−H bond arylation via photoredox/nickel dual catalysis. Sterically hindered chiral biimidazoline ligands are designed for this asymmetric cross-coupling reaction. Readily available alkyl benzenes and aryl bromides with various functional groups tolerance can be easily and directly transferred to useful chiral 1,1-diaryl alkanes including pharmaceutical intermediates and bioactive molecules. This reaction proceeds smoothly under mild conditions without the use of external redox reagents.
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spelling pubmed-66859912019-08-09 Enantioselective benzylic C–H arylation via photoredox and nickel dual catalysis Cheng, Xiaokai Lu, Huangzhe Lu, Zhan Nat Commun Article The asymmetric cross-coupling reaction is developed as a straightforward strategy toward 1,1-diaryl alkanes, which are a key skeleton in a series of natural products and bioactive molecules in recent years. Here we report an enantioselective benzylic C(sp(3))−H bond arylation via photoredox/nickel dual catalysis. Sterically hindered chiral biimidazoline ligands are designed for this asymmetric cross-coupling reaction. Readily available alkyl benzenes and aryl bromides with various functional groups tolerance can be easily and directly transferred to useful chiral 1,1-diaryl alkanes including pharmaceutical intermediates and bioactive molecules. This reaction proceeds smoothly under mild conditions without the use of external redox reagents. Nature Publishing Group UK 2019-08-07 /pmc/articles/PMC6685991/ /pubmed/31391466 http://dx.doi.org/10.1038/s41467-019-11392-6 Text en © The Author(s) 2019 Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/.
spellingShingle Article
Cheng, Xiaokai
Lu, Huangzhe
Lu, Zhan
Enantioselective benzylic C–H arylation via photoredox and nickel dual catalysis
title Enantioselective benzylic C–H arylation via photoredox and nickel dual catalysis
title_full Enantioselective benzylic C–H arylation via photoredox and nickel dual catalysis
title_fullStr Enantioselective benzylic C–H arylation via photoredox and nickel dual catalysis
title_full_unstemmed Enantioselective benzylic C–H arylation via photoredox and nickel dual catalysis
title_short Enantioselective benzylic C–H arylation via photoredox and nickel dual catalysis
title_sort enantioselective benzylic c–h arylation via photoredox and nickel dual catalysis
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6685991/
https://www.ncbi.nlm.nih.gov/pubmed/31391466
http://dx.doi.org/10.1038/s41467-019-11392-6
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AT luzhan enantioselectivebenzyliccharylationviaphotoredoxandnickeldualcatalysis